Self-assembling peptides: Implications for patenting in drug delivery andtissue engineering

Recent Patents on Drug Delivery and Formulation

Volumn 5, Issue 1, 2011, Pages 24-51

  Kumar, Pradeep ^a   Pillay, Viness ^a   Modi, Girish ^a   Choonara, Yahya E ^a   du Toit, Lisa C ^a   Naidoo, Dinesh ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Drug delivery; Patent; Peptide amphiphiles; Peptides; Self assembly; Tissue engineering

Indexed keywords

AMPHOPHILE; BIOMATERIAL; BONE MORPHOGENETIC PROTEIN 2; COLLAGEN; COPOLYMER; FIBRIN GLUE; FILLER; HYDROXYAPATITE; MATRIGEL; MOLECULAR SCAFFOLD; PEPTIDE; PEPTIDE DERIVATIVE; TISSUE SCAFFOLD; TRANSFORMING GROWTH FACTOR BETA1; NANOMATERIAL; PEPTIDOMIMETIC AGENT;

ALPHA HELIX; ARTICLE; BETA SHEET; BILAYER MEMBRANE; BIOMINERALIZATION; BONE TRANSPLANTATION; CELL ENCAPSULATION; DRUG DELIVERY SYSTEM; EQUIPMENT DESIGN; GEL; GENE DELIVERY SYSTEM; HEART INFARCTION; HYDROGEL; MATERIAL COATING; MICELLE; MOLECULAR RECOGNITION; MOLECULARLY TARGETED THERAPY; NANOFABRICATION; NERVE REGENERATION; PATENT; PRIORITY JOURNAL; PROTEIN STRUCTURE; REGENERATIVE MEDICINE; TISSUE ENGINEERING; TISSUE REGENERATION; WOUND DRESSING; CHEMISTRY; HUMAN; METABOLISM; PROSTHESES AND ORTHOSES; PROTEIN SECONDARY STRUCTURE; REVIEW;

DRUG DELIVERY SYSTEMS; HUMANS; NANOSTRUCTURES; PATENTS AS TOPIC; PEPTIDES; PEPTIDOMIMETICS; PROSTHESES AND IMPLANTS; PROTEIN STRUCTURE, SECONDARY; TISSUE ENGINEERING; TISSUE SCAFFOLDS;

EID: 79954448855     PISSN: 18722113     EISSN: 18722113     Source Type: Journal    
DOI: 10.2174/187221111794109510     Document Type: Article

References (107)

1. Zhang S. Emerging biological materials through molecular self assembly. Biotech Adv 2002; 20: 321-39.
2. Zhang S. Fabrication of novel biomaterials through molecular selfassembly. Nat Biotechnol 2003; 21: 1171-8.
3. Ulijn RV, Smith AM. Designing peptide based nanomaterials. Chem Soc Rev 2008; 37: 664-75.
4. Higashi N, Koga T. Self-assembled peptide nanofibers. Adv PolymSci 2008; 219: 27-68.
5. Petzelbauer, P., Reingruber, S., Pasteiner, W., Henning, R. Peptidesand peptide derivatives, the production thereof as well as their usefor preparing a therapeutically and/or preventively activepharmaceutical composition. WO2009137851 (2009).
6. Rudra JS, Tian YF, Jung JP, Collier JH. A self-assembling peptideacting as an immune adjuvant. Proc Natl Acad Sci USA 2010; 107:622-7.
7. Kriegel C, Arrechi A, Kit K, McClements DJ, Weiss J. Fabrication,functionalization, and application of electrospun biopolymernanofibers. Crit Rev Food Sci Nutr 2008; 48: 775-97.
8. Jung JP, Gasiorowski JZ, Collier JH. Fibrillar peptide gels inbiotechnology and biomedicine. Pept Sci 2010; 94: 49-59.
9. Behanna HA, Donners JJJM, Gordon AC, Stupp SI. Coassembly ofamphiphiles with opposite peptide polarities into nanofibers. J AmChem Soc 2005; 127: 1193-1200.
10. Paramonov SE, Jun H, Hartgerink JD. Self-assembly of peptideamphiphilenanofibers: The roles of hydrogen bonding andamphiphilic packing. J Am Chem Soc 2006; 128: 7291-8.
11. Smith AM, Williams RJ, Tang C, Coppo P, Collins RF, Turner ML, et al. Fmoc-diphenylalanine self assembles to a hydrogel via anovel architecture based on φ-φ interlocked β-sheets. Adv Mater 2008; 20: 37-41.
12. Gazit, E., Mahler, A., Reches, M. Self-assembled FMOC-FFhydrogels. US20090175785 (2009).
13. Löwik DWPM, van Hest JCM. Peptide based amphiphiles. Chem Soc Rev 2004; 33: 234-45.
14. Vankann M, Möllerfeld J, Ringsdorf H, Höcker H. Amphiphilicmodel peptides: Circular dichroism measurements andinvestigations by a langmuir balance. J Colloid Interface Sci 1996;178: 241-50.
15. von Maltzahn G, Vauthey S, Santoso S, Zhang S. Positivelycharged surfactant-like peptides self-assemble into nanostructures.Langmuir 2003; 19: 4332-7.
16. Rapaport H, Möller G, Knobler CM, Jensen TR, Kjaer K, Leiserowitz L, et al. Assembly of triple-stranded beta-sheetpeptides at interfaces. J Am Chem Soc 2002; 124: 9342-3.
17. Powers ET, Yang SI, Lieber CM, Kelly JW. Ordered langmuirblodgettfilms of amphiphilic β-hairpin peptides imaged by atomicforce microscopy. Angew Chem Int Ed 2002; 41: 127-30.
18. Xu G, Wang W, Groves JT, Hecht MH. Self-assembledmonolayers from a designed combinatorial library of de novo betasheetproteins. Proc Natl Acad Sci USA 2001; 98: 3652-7.
19. Schneider JP, Pochan DJ, Ozbas B, Rajagopal K, Pakstis L, Kretsinger J. Responsive hydrogels from the intramolecular foldingand self-assembly of a designed peptide. J Am Chem Soc 2002;124: 15030-7.
20. Epand RF, Lehrer RI, Waring A, Wang W, Maget-Dana R, Lelièvre D, et al. Direct comparison of membrane interactions ofmodel peptides composed of only Leu and Lys residues.Biopolymers 2003; 71: 2-16.
21. Hartgerink JD, Beniash E, Stupp SI. Self-assembly andmineralization of peptide-amphiphile nanofibers. Science 2001;294: 1684-8.
22. Wright ER, Conticello VP. Self-assembly of block copolymersderived from elastin- mimetic polypeptide sequences. Adv Drug Deliv Rev 2002; 54: 1057-73.
23. Li L, Charati MB, Kristi LK. Elastomeric polypeptide-basedbiomaterials. Polym Chem 2010 (in press). DOI:10.1039/b9py00346k.
24. Nowak AP, Sato J, Breedveld V, Deming TJ. Hydrogel formationin amphiphilic triblock copolypeptides. Supramol Chem 2006; 18:429-437.
25. Nowak AP, Breedveld V, Pakstis L, Ozbas B, Pine DJ, Pochan D, et al. Rapidly recovering hydrogel scaffolds from self-assemblingdiblock copolypeptide amphiphiles. Nature 2002; 417: 424-8.
26. Chécot F, Rodríguez-Hernández J, Gnanou Y, Lecommandoux S.pH-responsive micelles and vesicles nanocapsules based onpolypeptide diblock copolymers. Biomol Eng 2007; 24: 81-5.
27. Pauling L, Corey RB. The pleated sheet, a new layer configurationof polypeptide chains. Proc Natl Acad Sci USA 1951; 37: 251-6.
28. Zhang S, Holmes T, Lockshin C, Rich A. Spontaneous assembly ofa self-complementary oligopeptide to form a stable macroscopicmembrane. Proc Natl Acad Sci USA 1993; 90: 3334-8.
29. Boden, N., Aggeli, A., Mcleish, T.C.B. Beta sheet forming peptidesand gels made thereof. US0132974 (2002).
30. Dong H, Paramonov SE, Hartgerink JD. Self-assembly of a-helicalcoil-coiled nanofibers. J Am Chem Soc 2008; 130: 13691-5.
31. Moutevelis E, Woolfson DN. A periodic table of coiled-coil proteinstructures. J Mol Biol 2009; 385: 726-32.
32. Bromley EH, Sessions RB, Thomson AR, Woolfson DN. Designeda-helical tectons for constructing multicomponent syntheticbiological systems. J Am Chem Soc 2009; 131: 928-30.
33. Papapostolou D, Smith AM, Atkins ED, Oliver SJ, Ryadnov MG, Serpell LC, et al. Engineering nanoscale order into a designedprotein fiber. Proc Natl Acad Sci USA 2007; 104: 10853-8.
34. Xu C, Breedveld V, Kopecek J. Reversible hydrogels from selfassemblinggenetically engineered protein block copolymers.Biomacromolecules 2005; 6: 1739-49.
35. Zimenkov Y, Dublin SN, Ni R, Tu RS, Breedveld V, Apkarian RP, et al. Rational design of a reversible pH-responsive switch forpeptide self-assembly. J Am Chem Soc 2006; 128: 6770-6771.
36. Kyle S, Aggeli A, Ingham E, McPherson MJ. Production of selfassemblingbiomaterials for tissue engineering. Trends Biotechnol 2009; 27: 423-433.
37. Horii, A., Zhang, S., Wang, X., Gelain, F. Modified self assembling peptides. US20090162437 (2009).
38. Stupp, S.I., Guler, M.O. Branched peptide amphiphiles, relatedepitope compounds and self assembled structures thereof. US7452679 (2008).
39. Stupp, S.I., Donners, J.J.J.M., Silva, G.A., Behanna, H.A., Anthony, S.G. Branched peptide amphiphiles, related epitopecompounds and self assembled structures thereof. US7544661(2009).
40. Yokoi, H., Kinoshita, T. Self-assembling peptide and gel producedfrom the same. US20100016548 (2010).
41. Harrington DA, Cheng EY, Guler MO, Lee LK, Donovan JL, Claussen RC, et al. Branched peptide-amphiphiles as selfassemblingcoatings for tissue engineering scaffolds. J BiomedMater Res 2006; 78A: 157-67.
42. Stupp, S.I., Beniash, E., Hartgerink, J.D. Composition and methodfor self-assembly and mineralizatin of peptide amphiphiles.US7554021 (2009).
43. Chiti F, Dobson CM. Protein misfolding, functional amyloid andhuman disease. Annu Rev Biochem 2006; 75: 333-66.
44. Reches M, Gazit E. Casting metal nanowires within discrete self assembled peptide nanotubes. Science 2003; 300: 625-7.
45. Pingali V, Thiyagarajan P, Lynn DG. Nucleobase-directed amyloidnanotube self-assembly. J Am Chem Soc 2008; 130: 9829-35.
46. Santos SD, Chandravarkar A, Mandal B, Mimna R, Murat K, Saucede L, et al. Switch-peptides: Controlling self-assembly ofamyloid β-derived peptides in vitro by consecutive triggering ofacyl migrations. J Am Chem Soc 2005; 127: 11888-9.
47. Blake C, Serpell L. Synchrotron X-ray studies suggest that the coreof the transthyretin amyloid fibril is a continuous beta-sheet helix. Structure 1996; 4: 989-98.
48. Mi K, Wang G, Liu Z, Feng Z, Huang B, Zhao X. Influence of aself-assembling peptide, RADA16, compared with collagen I andmatrigel on the malignant phenotype of human breast-cancer cellsin 3D cultures and in vivo. Macromol Biosci 2009; 9: 437-43.
49. Tabesh H, Amoabediny G, Nik NS, Heydari M, Yosefifard M, Siadat SO, et al. The role of biodegradable engineered scaffoldsseeded with Schwann cells for spinal cord regeneration.Neurochem Int 2009; 54: 73-83.
50. Matrigel. Available at: http://en.wikipedia.org/wiki/Matrigel(Accessed on: July 19, 2010).
51. Alovskaya A, Alekseeva T, Phillips JB, King V, Brown R. Fibronectin, collagen, fibrin - Components of extracellular matrixfor nerve regeneration. In: Ashammakhi N, Reis RL, Chiellini E,Eds. Top Tissue Eng. Milton Keynes: Biomaterials and Tissue EngGroup 2007: VII(1-26).
52. Valentin AH, Weber J. Receptor technology - cell binding to P-15:A new method of regenerating bone quickly and safely-preliminaryhistomorphometrical and mechanical results in sinus flooraugmentations. Keio J Med 2004; 53: 166-71.
53. Qian JJ, Bhatnagar RS. Enhanced cell attachment to anorganicbone mineral in the presence of a synthetic peptide related tocollagen. J Biomed Mater Res 1996; 31: 545-54.
54. Bhatnagar RS, Qian JJ, Wedrychowska A, Sadeghi M, Wu YM, Smith N. Biomimetic habitats for cells: Ordered matrix depositionand differentiation in gingival fibroblasts cultured onhydroxylapatite coated with a collagen analogue. Cell Mater 1999;9: 93-104.
55. Bhatnagar, R.S. Synthetic compounds and compositions withenhanced cell binding. US5354736 & US6818620 (2004).
56. Yukna RA, Krauser JT, Callan DP, Evans GH, Cruz R, Martin M.Multi-center clinical comparison of combination anorganic bovinederivedhydroxyapatite matrix (ABM)/cell binding peptide (P-15)and ABM in human periodontal osseous defects. 6-month results. JPeriodontol 2000; 71: 1671-1679
57. Yukna RA, Krauser JT, Callan DP, Evans GH, Cruz R, Martin M. Thirty-six month follow-up of 25 patients treated with combinationanorganic bovine-derived hydroxyapatite matrix (ABM)/cellbindingpeptide (P-15) bone replacement grafts in human infrabonydefects. I. Clinical findings. J Periodontol 2002; 73: 123-8.
58. Rodriguez-Cabello JC, Reguera J, Girotti A, Alonso M, Testera AM. Developing functionality in elastin-like polymers byincreasing their molecular complexity: The power of the geneticengineering approach. Prog Polym Sci 2005; 30: 1119-45.
59. Chilkoti A, Christensen T, MacKay JA. Stimulus responsive elastinbiopolymers: Applications in medicine and biotechnology. CurrOpin Chem Biol 2006; 10: 652-7.
60. Malafaya PB, Silva GA, Reis RL. Natural-origin polymers ascarriers and scaffolds for biomolecules and cell delivery in tissueengineering applications. Adv Drug Deliv Rev 2007; 59: 207-33.
61. Available at: http://en.wikipedia.org/wiki/Tissueengineering(Accessed on: July 19, 2010).
62. 3Dm Medical Technology. Available at: http://www.3dmatrix.co.jp/dl_file/PuraMatrix_Introduction.pdf (Accessed on:July 19, 2010).
63. Kisiday J, Jin M, Kurz B, Hung H, Semino C, Zhang S, et al. Selfassemblingpeptide hydrogel fosters chondrocyte extracellularmatrix production and cell division: Implications for cartilagetissue repair. Proc Natl Acad Sci USA 2002; 99(15): 9996-10001.
64. Horii A, Wang X, Gelain F, Zhang S. Biological designer selfassemblingpeptide nanofiber scaffolds significantly enhanceosteoblast proliferation, differentiation and 3D migration. PLoSOne 2007; 2: 190.
65. Misawa H, Kobayashi N, Soto-Gutierrez A, Chen Y, Yoshida A, Rivas-Carrillo JD, et al. PuraMatrix facilitates bone regeneration inbone defects of calvaria in mice. Cell Transplant 2006; 15: 903-10.
66. Ellis-Behnke RG, Liang YX, You SW, Tay DK, Zhang S, So KF, et al. Nano neuro knitting: Peptide nanofiber scaffold for brainrepair and axon regeneration with functional return of vision. ProcNatl Acad Sci USA 2006; 103: 5054-9.
67. Kretsinger JK, Haines LA, Ozbas B, Pochan DJ, Schneider JP. Cytocompatibility of self-assembled beta-hairpin peptide hydrogel surfaces. Biomaterials 2005; 26: 5177-86.
68. Bilic R, Simic P, Jelic M, Stern-Padovan R, Dodig D, vanMeerdervoort HP, et al. Osteogenic protein-1 (BMP-7) accelerateshealing of scaphoid non-union with proximal pole sclerosis. IntOrthop 2006; 30: 128-34.
69. Lee KY, Mooney DJ. Hydrogels for tissue engineering. Chem Rev 2001; 101: 1869-1879.
70. Seubert, R., Tanczos, E. Method and compositions for producingcell transplants. WO040444 (2001).
71. Fields, G.B., Tirrell, M.V. Reversible hydrogels from selfassemblingartificial proteins. US6096863 (2000).
72. Zhang, S., Rich, A., Yan, L., Whitesides, G. Substrate selfassemblingpeptide surfaces for cell patterning and interactions.US6368877 (2002).
73. Zhang, S., Lockshin, C., Rich, A., Holmes, T. Stable macroscopicmembranes formed by self-assembly of amphiphilic peptides anduses therefore. US6548630 (2003).
74. Holmes, T., Zhang, S., Rich, A., Dipersio, M.C., Lockshin, C. Stable macroscopic membranes formed by self-assembly ofamphiphilic peptides. US6800481 (2004).
75. Valluzzi, R., Kaplan, D. Self-assembling polymers, and materialsfabricated therefrom. US20050090641 (2005).
76. Stupp, S.I., Niece, K.L., Hartgerink, J.D. Self-assembled peptideamphiphiles& self-assembled peptide nanofiber networkspresenting multiple signals. US20050272662 (2005).
77. Haynie, D.T. Method for designing polypeptides for thenanofabrication of thin films. WO2006057633 (2006).
78. Ellis-Behnke, R., Schneider, G., Zhang, S. Self-assemblingpeptides for regeneration and repair of neural tissue.US20050287186 (2005).
79. Lee, R.T., Davis, M.E. Targeted delivery of biological factors usingself-assembling peptide nanofibers. US20060088510 (2006).
80. Boden, N., Agelli, A., Ingham, E., Kirkham, J. Beta sheet tapesribbons in tissue engineering. US7700721 (2010).
81. Stupp, S.I., Kessler, J.A. Methods and compositions forencapsulation of cells. US20060247165 (2006).
82. Spirio, L., Chu, Z. Purified amphiphilic peptide compositions anduses thereof. US20060084607 (2006).
83. Michal, E., Basu, S., Kuo, H.C. Methods and compositions fortreating post-myocardial infarction damage. US20070218118 (2007).
84. Ozbas, B., Kretsinger, J., Butterick, L.A., Rajagopal, K., Pochan, D.J., Schneider, J.P. Novel hydorgels and uses thereof.US20070128175 (2007).
85. Luo, D., Um, S.H. Nucleic acid-based matrixes for proteinproduction. US20070117177 (2007).
86. Young, M.J., Douglas, T., Idzerda, Y.U. Protein cages for thedelivery of medical imaging and therapeutic agents viral capsidprotein. US20070059245 (2007).
87. Ellis-Behnke, R., Norchi, T., Kelly, S.R. Compositions forprevention of adhesions and other barrier applications.US20080032934 (2008).
88. Stupp, S.I., Spoerke, E.D., Anthony, S.G., Niece, K.L. Methodsand materials for nanocrystalline surface coatings and attachmentof peptide amphiphile nanofibers thereon. US7390526 (2008).
89. Lee, R.T., Hsieh, P. Sustained delivery of PDGF using selfassemblingpeptide nanofibers. US7429567 (2008).
90. Harris, I.R., Harmon, A.M., Brown, L.J., Gosiewska, A. Tissueengineeringscaffolds containing self-assembled-peptide hydrogels.US20080145934 (2008).
91. Capito, R.M., Azevedo, H.S., Stupp, S.I. Self-assemblingmembranes and related methods thereof. US20080199431 (2008).
92. Stupp, S.I., Donners, J.J.J.M., Silva, G.A., Behanna, H.A.,Anthony, S.G. Self-assembling peptide amphiphiles and related methods for growth factor delivery. US7544661 (2009).
93. Rapaport, H. Amphiphilic peptides and hydrogel matrices thereof for bone repair. US20100015197 (2010).
94. Stupp, S.I., Hartgerink, J.D., Beniash, E. Self-assembly of peptideamphiphilenanofibers under physiological conditions. US7745708(2010).
95. Diwan, A., Onton, A.L., Tatake, J.G. Self assembling amphiphilicpolymers as antiviral agents. US20100008938 (2010).
96. Zhang S, Lockshin C, Cook R, Rich A. Unusually stable β-sheetformation of an ionic self-complementary oligopeptide. Biopolym 1994; 34: 663-672.
97. Zhang S, Holmes T, DiPersio M, Hynes RO, Su X, Rich A. Selfcomplementaryoligopeptide matrices support mammalian cellattachment. Biomaterials 1995; 16: 1385-93.
98. Aggeli A, Boden N, Cheng YL, Findlay JB, Knowles PF, Kovatchev P, et al. Peptides modeled on the transmembrane regionof the slow voltage-gated IsK potassium channel: Structuralcharacterization of peptide assemblies in the beta-strandconformation. Biochemistry 1996; 35: 16213-16221.
99. Aggeli A, Bell M, Boden N, Keen JN, Knowles PF, McLeish TCB, et al. Responsive gels formed by the spontaneous self-assembly ofpeptide into polymeric β-sheet tapes. Nature 1997; 386: 259-62.
100. Aggeli A, Bell M, Carrick LM, Fishwick CW, Harding R, Mawer PJ, et al. pH as a trigger of peptide β-sheet self-assembly andreversible switching between nematic and isotropic phases. J AmChem Soc 2003; 125: 9619-28.
101. United States Patent and Trademark Office. Available on:http//www.uspto.gov/patft/index.html (Accessed on: 29 July,2010).
102. Aggeli A, Bell M, Boden N, Harding R, McLeish TCB, Nyrkova I, et al. Exploiting protein folding and misfolding to engineer novelnanostructured materials. Biochemist 2000; 22: 10-14.
103. Nyrkova IA, Semenov AN, Aggeli A, Bell M, Boden N, McLeish TCB. Self-assembly and structure transformations in livingpolymers forming fibrils. Eur Phys J 2000; 17: 499-513.
104. Aggeli A, Nyrkova IA, Bell M, Harding R, Carrick L, McLeish TC, et al. Hierarchical self-assembly of chiral rod-like molecules asa model for peptide β-sheet tapes, ribbons, fibrils, and fibres. ProcNatl Acad Sci USA 2001; 98: 11857-62.
105. Kirkham J, Firth A, Vernals D, Boden N, Robinson C, Shore RC, et al. Self-assembling peptide scaffolds promote enamel remineralization. J Dent Res 2007; 86: 426-30.
106. Firth A, Aggeli A, Burke JL, Yang X, Kirkham J. Biomimetic selfassemblingpeptides as injectable scaffolds for hard tissueengineering. Nanomed 2006; 1: 189-99.
107. Bell CJ, Carrick LM, Katta J, Jin Z, Ingham E, Aggeli A, et al.Self-assembling peptides as injectable lubricants for osteoarthritis.J Biomed Mater Res A 2006; 78: 236-46.